Linoleic Acid
Structural Formula Vector Image
Title: Linoleic Acid
CAS Registry Number: 60-33-3
CAS Name: (Z,Z)-9,12-Octadecadienoic acid
Additional Names: 9,12-linoleic acid; linolic acid
Molecular Formula: C18H32O2
Molecular Weight: 280.45
Percent Composition: C 77.09%, H 11.50%, O 11.41%
Literature References: An essential fatty acid. Major constituent of many vegetable oils, e.g., cottonseed, soybean, peanut, corn, sunflower seed, safflower, poppy seed, linseed, and perilla oils, where it occurs as a glyceride. Characteristic ingredient of semi-drying oils. Isoln: Swern, Parker, J. Am. Oil Chem. Soc. 30, 5 (1953); Parker et al., Biochem. Prep. 4, 86 (1955); McCutcheon, Org. Synth. coll. vol. III, 526 (1955). Summary of work on structure: T. P. Hilditch, The Chemical Constitution of Natural Fats (Chapman & Hall, London, 2nd ed. 1956). Synthesis: Raphael, Sondheimer, J. Chem. Soc. 1950, 2102; Gensler, Thomas, J. Am. Chem. Soc. 73, 4601 (1951); Walborsky et al., ibid. 2590; Nigam, Weedon, J. Chem. Soc. 1956, 4052; Osbond, Wickens, Chem. Ind. (London) 1959, 1288. Review of physiological role in mammals: H. S. Hansen, Trends Biochem. Sci. 11, 263 (1986).
Properties: Colorless oil. Easily oxidized by air, cannot be distilled without decompn. Storage in ester form is recommended. d418 0.9038; d422 0.9007. mp -12°. bp1.4 202°; bp16 230°. nD11.5 1.4715; nD20 1.4699; nD21.5 1.4683; nD50 1.4588. Iodine value: 181.1. Thiocyanogen value 96.7. Freely sol in ether. Sol in abs alc. One ml dissolves in 10 ml petr ether. Miscible with dimethylformamide, fat solvents, oils.
Melting point: mp -12°
Boiling point: bp1.4 202°; bp16 230°
Index of refraction: nD11.5 1.4715; nD20 1.4699; nD21.5 1.4683; nD50 1.4588
Density: d418 0.9038; d422 0.9007
Derivative Type: Aluminum salt
CAS Registry Number: 645-17-0
Molecular Formula: Al(C18H31O2)3
Molecular Weight: 865.29
Percent Composition: Al 3.12%, C 74.95%, H 10.83%, O 11.09%
Properties: Yellow lumps or powder; linseed oil odor. Practically insol in water. Sol in oils, fixed alkali hydroxides.
Derivative Type: Methyl ester see Methyl Linoleate
Derivative Type: Ethyl ester see Ethyl Linoleate
Derivative Type: Cyclohexylamide
CAS Registry Number: 3207-50-9
Additional Names: Linolexamide; N-cyclohexyllinoleamide
Trademarks: Clinolamide
Molecular Formula: C24H43NO
Molecular Weight: 361.60
Percent Composition: C 79.72%, H 11.99%, N 3.87%, O 4.42%
Use: Manuf paints, coatings, emulsifiers, vitamins. Aluminum salt used to manuf lacquers.
Therap-Cat: Nutrient (essential fatty acid).
Therap-Cat-Vet: Dietary supplement.

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